The Victory Lap​

In late 2016, I was sitting on the worn wooden floor of a small house in Bloomfield New Jersey with a coach I’d been working with for most of the year. A true Digital Nomad, she had been merely a virtual presence for our sessions until this final one — both of us being from New Jersey, she offered to do one in-person intensive super-session. The timing was convenient: days away from the new year, I wanted to reflect on my last year and my goals for the next.

Much of our conversation revolved around the themes of embracing imperfection and creative expression — after a year of working with me, my coach was well aware of my overthinking, perfectionistic tendencies and how often they got in my way of doing more writing and undertaking more creative work.

We brainstormed ideas for how I could improve at both of these and somewhere in there was the nugget that would become my first 75 days of the year, where I’d highlight a #dailymistake from my day.

This was the first post:

My friend, Christine, challenged me to live more vulnerably and expressively in 2017. Here it goes —

Social media is a place for the ‘highlight reels,’ the filtered, best-of-the-best, wittiest, most golden thoughts and moments. Rarely is it a place where personal failure, undone-ness, and other inconvenient feelings make their way to the surface (except in political and social justice op-eds)

Every day, I am challenging myself to share something about mistake I’ve made that day to balance out the more careful, overly-deliberate persona I have on social media. Some mistakes will be boring. Some will be next-level ridiculous. Some will be sad. Many will be relatable, and, I hope, offset the potential that the my daily posting becomes insufferable.

I hope to come out of 2017 taking myself a little less seriously and being more comfortable being unabashedly myself in public — internet included. If you’re reading these, I hope you’ll be entertained and maybe a little bit inspired to share some mistakes of your own with the world…

Over the next few months, the mistakes ranged from totally mundane to completely absurd, the more personal to the more professional.

Some from the archives that were a little more serious:

February 20: allowing myself to live in fear of a number on the scale.

March 9: feeling afraid, ashamed, or otherwise unable to ask for help when I know I need it.”

January 10: having to shut down a project one of my engineers had in the pipeline for 2 months because of important questions from other teams that surfaced too late in the game. Had I engaged my cross-functional partners sooner or more often in the building process, we could have addressed the other teams’ concerns early on and saved the work. Still so much to learn in #productmanagement

And others that were a little funnier:

January 13: Walking into Sephora on payday. My checking account never stood a chance. If you can’t dress like a million bucks, put your best face forward?

January 30: spent all day crafting and editing an important email to about 100 people. Noticed after sending that I began the email with “Happy Tuesday” when it is definitely not Tuesday yet.

January 26: #tbt to that night shaving my legs in the bathroom of a bar earlier in this month. Lesson: shaving your legs — no matter your romantic prospects the rest of the evening — is never that urgent. If anything, in the confines of a bar bathroom, it can be dangerous.

About 2.5 months in, though, I went for a switch from mistakes to victories. My execution was clumsy and lacked a decent explanation:

March 15: ignoring the feedback the first few times that it was time for a more positive rebrand of this daily practice.

March 16: becoming ready and willing to acknowledge that feedback and to make a change in a more positive direction.

The truth of it is, more than getting random crap from people for the mistakes, the real reason I ended up switching was because I was feeling sad. I ended up overly-focused on the mistake I made that day instead of the thing I learned from the mistake. Instead of coming to the end of the day to think of something positive that happened, identifying mistakes every day just stoked the flame of my inner critic. Even though, at the end of it, it’s just a matter of terms (I could have called this experiment a #dailylesson or #whatilearnedtoday or some other hashtag) but the reality was I was in a dark mental space at the time. I wasn’t in a position to see many of the things happening in my life as much growth opportunities so much as ways in which I was “not enough” and a “f***-up.”

I spent the next 3.5 months writing about little wins from my day to day instead. Even though most days the reality is getting through the day was my #littlevictory, I came up with some more creative ones:

March 30: the political climate in America may be dark and stormy, but it can’t put a damper on the rainbows and light in the Castro.

April 5: saying something that turned a dear friend’s day around, making her laugh so hard she forgot why she had been sad.

May 15: Saturday me, knowing Monday me was going to have a rough day, ordering gifts off my Amazon wish list to come home to on Monday night. I’ve never been so happy to see two books of poetry, five new sports bras, and a new pair of shoes.

June 16: conversation with a peer tonight at the gym, with me approaching a 3-month anniversary with jiujitsu: “You’ve gotten a whole lot better since you first stepped on the mat.” 🙌

And possibly my favorites:

June 19: actually being able to wear a bridesmaid’s dress again for an occasion other than the wedding for which it was purchased and tailored. I’m convinced this rarely — if ever — happens.

June 27: becoming the proud owner of a Le Creuset Dutch Oven, or “losing yet another reason to get married because I just acquired the thing I’d have wanted most off a registry.” Stephen and Daniel — props to you both and Nick for the rewards bucks that made this purchase happen.

There were multiple posts about jiujitsu and Keytar Bear and cooking — if I’m being truly honest, I don’t do much with my life in Boston anymore aside from roll, seek out the Bear, and cook things. And maybe go on a few ridiculous dating adventures from time to time. That’s about as interesting as I get.

Why stop the #littlevictory train? Because if I’m being true to myself, I’ve reached a point in this experiment where it’s feeling more forced than fun to come up with things that are a win for the day.

So in that spirit, the final #littlevictory here is knowing when a good thing has come to an end and it’s time to move on. But not without reflecting on it a little bit — hence this blog post.

Here’s what I learned from this experience.

You never know what will resonate with people. You also don’t know who and what people will read. There were posts that I expected to strike a chord that fell completely flat and others that exploded with likes that made me ask, “Really? That one?” There were days where I had people I rarely speak to reach out with a direct message to say something kind — or in the case of one person, to call me a bitch. I promptly blocked that person.

Achieving and sustaining any measure of internet influence is difficult. I’m convinced that the only way I’ll be able to start a real movement on social media is by getting cast on a reality television show and endosing slimming teas and tooth whiteners. That said, perhaps I hadn’t been giving enough credit to the Twitter pundits and Instagram influencers who do this kind of content creation work for a living: coming up with something fresh, on brand, relevant, and authentic on social media with meaningful consistency is a challenge.

I became absurdly addicted to Facebook ‘likes’ and reactions — more than I thought I would be. It became easy to treat these as a reflection of how many people care, instead of as the product of an algorithm into which friends’ behavior have only so much input. I noticed myself becoming competitive with myself regarding the posts, feeling withdrawal when I came off a day with lots of likes and was met by very few the following day. It was problematic, because it was this kind of thinking that threatened to undermine the spirit of ingenuity and whimsy on which the #dailymistake and #littlevictory were based.

Social media is exhausting — both contributing to it and consuming it. So now I’ll be going back to posting when I feel like I really have something to say. Maybe daily, maybe rarely. Social media is just another tool for documenting and sharing. Sometimes it brings us together, sometimes it distances us. I still don’t know the right balance of including it in my day to day.

All I know for sure is that we don’t need posts or pictures to affirm to ourselves or prove to others that we’re “winning” or losing at life. It’s not a game, but a journey, right?